Reaction products of a polyglycidyl ether of a polyphenol and an amino acid and aqueous solubilized products therefrom

Abstract

Coating compositions which may be applied by conventional techniques as well as by electrodeposition are provided by reacting a polyglycidyl ether of a polyphenol with an amino acid containing at least one amine group and one carboxyl group, wherein the amine group of the acid is preferentially reactive with the epoxy groups of the polyglycidyl ether. The resultant product can then be solubilized by neutralizing at least a portion of the acid functionality thereof with an amine or other base. Especially useful amino acids are the aminobenzoic acids.

We claim: 
     
       1. An anionic aqueous composition comprising water and (1) an at least partially based neutralized reaction product of: (a) a polyglycidyl ether of a polyphenol having a 1,2-epoxy equivalency greater than 1.0; and   (b) an aromatic amino acid selected from the class consisting of anthranilic acid, p-aminobenzoic acid, m-aminobenzoic acid, 3-amino-p-toluic acid, 3-aminosalicylic acid, 3-amino-4-methoxybenzoic acid, 6-amino-m-toluic acid, 3-amino-4-chlorobenzoic acid, 2-amino-5-nitrobenzoic acid, 2-nitro-5-aminobenzoic acid, 5-aminoisophthalic acid;      said reaction product having unreacted carboxylic acid groups which are neutralized with base to form anionic salt groups,   (2) a curing agent for said reaction product selected from the class consisting of aminoplast resins, phenoplast resins or blocked or semi-blocked polyisocyanates.   
     
     
       2. The aqueous composition of claim 1 wherein the equivalent ratio of epoxy groups in said polyglycidyl ether to amine groups in said amino acid is between 1:0.20 and 1:1.25. 
     
     
       3. The aqueous composition of claim 1 wherein said reaction product is at least partially neutralized with a volatile base. 
     
     
       4. The aqueous composition of claim 3 wherein said base is an amine. 
     
     
       5. The aqueous composition of claim 1 wherein said polyphenol is bisphenol A. 
     
     
       6. The aqueous composition of claim 1 wherein said amino acid is anthranilic acid. 
     
     
       7. The aqueous composition of claim 1 wherein said amino acid is p-aminobenzoic acid. 
     
     
       8. The aqueous composition of claim 1 wherein said amino acid is m-aminobenzoic acid. 
     
     
       9. An anionic aqueous composition comprising water and: (1) an at least partially base neutralized reaction product of: (a) a polyglycidyl ether of a polyphenol having a 1,2-epoxy equivalency of greater than 1.0; and   (b) an aromatic amino acid selected from the class consisting of anthranilic acid, p-aminobenzoic acid, m-aminobenzoic acid, 3-amino-p-toluic acid, 3-aminosalicylic acid, 3-amino-4-methoxybenzoic acid, 6-amino-m-toluic acid, 3-amino-4-chlorobenzoic acid, 2-amino-5-nitrobenzoic acid, 2-nitro-5-aminobenzoic acid, 5-aminoisophthalic acid;      said reaction product having unreacted carboxylic acid groups which are neutralizable with base to form anionic salt groups;   (2) a resin selected from the group consisting of hydrocarbon resins, water-soluble acrylic resins, acrylic polymer emulsions, aqueous dispersions of amide-containing acrylic interpolymers, or combinations thereof; and   (3) a curing agent selected from the class consisting of aminoplast resins, phenoplast resins, blocked or semiblocked polyisocyanates.   
     
     
       10. The aqueous composition of claim 9 wherein said composition based on total weight of (1) and (2) contains from about 5 to about 95 percent by weight of (1) and from about 95 to about 5 percent by weight of (2). 
     
     
       11. The aqueous composition of claim 9 wherein said resin is an acrylic polymer emulsion. 
     
     
       12. The aqueous composition of claim 9 wherein said resin is an aqueous dispersion of an amide-containing acrylic interpolymer. 
     
     
       13. The aqueous composition of claim 9 further containing a pigment or pigments.